It appears to be a means to an end and the path of least resistance (somewhat related to number 1).

Taking small, manageable steps now will help you make informed decisions when you're ready to invest.Good luck!

 @Greg Abel I think it's important to consider the long-term, as changing property management software is difficult.

I have some flexibility but rely heavily on my team for admin work and the day-to-day operations of property management.

The manager doesn't determine what they do and don't like, they 'manage' the HOA to comply with the law and guidance from the Board.

I work with a property management company in NJ and we see a lot of success with our clients holding long-term rentals. https://www.tvdhousing.com/Welcome to BP! 

If you're willing and able, I do recommend the "house hacking" strategy which is just a fancy name for buying a rental property and living in one of the units, because you'll get very favorable financing - an owner-occupied fixed-rate 30-year mortgage.I'd also say, analyze that property as if you won't live there and it's a pure rental, and make sure the property is still cash flow positive if there's a tenant in your unit because then you'll know if it's actually a good investment.And when you analyze it, include payment of a property manager in your #s because if you don't, and doing so would make it go cash flow negative, then you've just bought yourself a job because you literally can't step away from managing it without losing money.

For this reason, I don't see there being a good pool of tenants or a ton of demand considering the economy is so slow and people who spend time and $ there typically have vacation homes there.The fires certainly have not helped, and I know they have had moratoriums for Home insurance in the region.That being said, for a place to purchase acreage, it still is relatively cheap compared to that of other wine country atmospheres and can have all the same charm.

I'm meeting with a couple agents i was referred to through my network and am wondering what critical questions I should be asking them to understand if they are the right partners for me in this market, especially considering I will be managing this investment from the other side of the country, and what info I should be prepared to provide to them.

Set your investment criteria, systems, and rules—and stick to them.2.Tenant management is all about structure.